Formal [4+1] annulations of salicylaldehydes with <scp>3‐chlorooxindoles</scp> for diastereoselective construction of dihydrobenzofuranspirooxindoles by solvent‐free grinding-Reference-Cited by-同舟云学术

Formal [4+1] annulations of salicylaldehydes with 3‐chlorooxindoles for diastereoselective construction of dihydrobenzofuranspirooxindoles by solvent‐free grinding

Published:2023-05-18 Issue:10 Volume:60 Page:1809-1814
ISSN:0022-152X
Container-title:Journal of Heterocyclic Chemistry
language:en
Short-container-title:Journal of Heterocyclic Chem

Author:

Li Yue¹,Wang Feng¹,Ning Rui¹,Kong Dulin²,Wu Mingshu¹^ORCID

Affiliation:

1. Key Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, College of Chemistry & Chemical Engineering Hainan Normal University Haikou Hainan Province People's Republic of China

2. Hainan Key Laboratory for Research and Development of Tropical Herbs, School of Pharmacy Hainan Medical University Haikou Hainan People's Republic of China

Abstract

AbstractA highly diastereoselective solvent‐free grinding approach for the construction of dihydrobenzofuranspirooxindole derivatives through a formal [4+1] annulations of α‐chlorooxindoles with salicylaldehydes in the presence of Brønsted base is reported. This transformation proceeds by Darzens‐type epoxidation to give trans‐form spiro‐epoxyoxindoles, followed by the nucleophilic ring‐opening/an intramolecular cyclization, providing cis‐form dihydrobenzofuran frameworks.

Publisher

Wiley

Subject

Organic Chemistry

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/jhet.4674

Reference33 articles.

1. Recent advances in organocatalytic asymmetric multicomponent cascade reactions for enantioselective synthesis of spirooxindoles

2. Spirooxindoles as Potential Pharmacophores

3. The use of spirocyclic scaffolds in drug discovery

4. Synthesis and antifungal activities of novel polyheterocyclic spirooxindole derivatives

5. Discovery of core-structurally novel PTP1B inhibitors with specific selectivity containing oxindole-fused spirotetrahydrofurochroman by one-pot reaction

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